Cr(III), Fe(II), Ni(II), Co(II), and Cu(II) complexes of a symmetric Schiff base ligand (L), N'-1-(2-(p-tolyl) hydrazono) propan-2-ylidene)-2-1-(2-(p-tolyl)hydrazono) propan-2 ylidene) hydrazine-1-carbothiohydrazide have been synthesized. Elemental analysis, UV-Visible, FT-IR, mass spectra, magnetic susceptibility, and conductometric techniques were used to characterise the ligand and its metal complexes. Gram-positive bacteria (Staphylococcus aureus, Staphylococcus faecalis, and Bacillus subtilis), Gram-negative bacteria (Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Escherichia coli), and fungi were used to assess the antibacterial activity of the presented compounds (Candida alibicans). The synthesized complexes displayed potential antibacterial activity when evaluated by the in vitro approach against various bacterial and fungal strains. Comparing all of the studied species, Co(II) complex exhibits the highest activity versus all tested organisms. Based on the DFT level, structural characteristics and MEP of the synthesized compounds were computed and correlated with the experimental results. To determine the most favoured mode of interaction, molecular docking studies with a few chosen protein structures have been carried out using the DFT-optimized structures of the Schiff base and its Co(II) complex.